


The Holiday

by Notmenotthemtwo



Category: Supernatural
Genre: Carnival, Day At The Beach, F/M, Falling In Love, Heartbreak, Kissing, Slow Dancing
Language: English
Status: Completed
Published: 2020-09-29
Updated: 2020-09-29
Packaged: 2021-03-07 18:02:40
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 2,417
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26711881
Author URL: https://archiveofourown.org/users/Notmenotthemtwo/pseuds/Notmenotthemtwo
Summary: Dean and Ruby spend a fun filled holiday together. Not enemies, but something else.
Relationships: Ruby/Dean Winchester
Kudos: 1





	1. Chapter 1

Dean and Ruby were on some random beach somewhere holding hands. Dean told Sam he had to  
see a old friend. He wasn't wrong, but "friend" is so wrong. "Fiend" is a better word. He would never admit it, he was enjoying Ruby's company. Nothing like true honesty in their "relationship." 

Sam protested and insisted on coming, but Dean convinced him to help Bobby with a hunt he had trouble working on. Rufus Turner wasn't available, he had his own thing going on. Sam reluctantly agreed. But he always wondered where Dean goes. Lilith was out there. He also wondered why Ruby wouldn't answer his calls or texts. Castiel left Dean alone. Ruby gave him a charm to hide from all angels and demons.

Ruby gives Dean a appreciative look. Damn. With those shorts, hat and sunglasses, Dean was a babe. That necklace made him look hot. Mmm. Dean must have noticed, he pulled her closer and planted a kiss on her dark hair. He loved her outfit, a red bikini. Dental floss would cover her better.

They held each other walking down the beach. Here they weren't Dean the hunter or Ruby the demon bitch. Here he was Winchester and Ruby the demon woman. Ruby loved this. For once she didn't have to obey Lilith's orders, she could have fun. She liked Dean, she really did. Whenever they saw each other, they "dated." They banged as well, but sex was fun. With her and Sam, it was part of her job. Sam was good, but he had no idea who she was. Dean at least understood her. She looked up at Dean and asked for a kiss. He complied and stopped. He smiles down at her and kisses her. A real kiss, not a casual peck. If anyone saw them, they would think they were a couple. 

Ruby sighs as he holds her in his arms. She pulled him close and hugs him. She hoped she wasn't falling in love. She squashed the thought. This was just a casual thing. She closed her vessel's eyes and listened to Dean's heart. So alive. So rhythm. She smiled at the sound. The spell broke when Dean suggested they go play in the water.

So they did. Ruby was screaming happily when Dean was chasing her down the beach. He was laughing saying she was going to be thrown into the cold lake.

"Don't you dare, Winchester!" She yells laughing.

"Too late!" He grabs her and swings her around. 

She screamed when he picked her up and threw her in the cold water.

"You asshole!" She says wiping her eyes. She pretended to be mad when he was laughing. 

They played in the water for awhile. Afterwards while he was laying on his towel, napping, Ruby bribed a kid with five bucks to borrow his bucket. She could have stolen it, but whenever she was with Dean, she had to be on the straight and narrow. It sucked, but she didn't mind. 

She goes to the water and filled it with water. She then sneaked towards Dean to splash him, unfortunately Dean's hunter instincts were deeply ingrained. He got up quickly and seeing what Ruby was going to do, he looked annoyed. He then gives Ruby a smirk.

"You forget, my instincts are razor sharp." 

Ruby smirks at him. She splashed the contents of the water on him. She ran when Dean was wiping his eyes.

"You bitch! Run! When I get my hands on you!" He threatened.

"Ha! Tough words! C'mon!" She taunts him by using her finger. She screamed when he chases her, catching her a few seconds later. 

They had fun all afternoon. They built a sandcastle, rented a kite, and shared a sundae. Dean couldn't remember when he had so much fun. He found himself liking her. Ruby must have felt the same way. She held his hand. They stared at each other holding each other's hand. Dean intertwines his fingers with hers. 

Just today. They were just two people having fun.


	2. Chapter 2

They went to a "romantic" restaurant. Romantic for Dean anyway. It was a run down dump, but Dean loved the bacon cheeseburgers. Ruby was disappointed, but where Sam took her on their meetings were dull. Coffee shops and diners. Yawn. 

Dean swore this restaurant was a hidden gem. The food was out of this world. He wasn't kidding, Ruby loved the shrimp basket she ordered. She also ordered saltless fries and both were drinking beers. 

"Cheers."

"Cheers."

They click the bottles. Dean then asked her to dance. A oldie his parents listened too, "Georgia on my Mind.''

It was cheesy, but Ruby didn't mind. The restaurant was empty so they had the whole place to themselves. They danced holding each other's hand, with the other one on their waists. The cook and his wife came and joined them.

They stared at each other's eyes. Ruby wanted to run. She was scared what she was feeling. She felt horrified when she felt a single tear. Dean wiped it away.

"Don't. Tomorrow isn't here yet. Just tonight."

Ruby could barely see. Dean just held her. They danced closer just swaying to the music. Ruby felt afraid. But she forced herself to push her feelings down. She said she wanted to go. Dean didn't argue. His heart was beating fast.

They paid and tipped generously. Dean and her drove not saying anything. They both knew this "thing" they were having was never going to blossom. After her mission was over, she was dead. Dean knew it too. 

Ruby closed her eyes. Tomorrow didn't happen yet. They had a few days left. Fuck it. Dean and her, they had each other. At least for a few days. She asked him to pull over.

"Winchester. This thing..."

"I know."

"It can never be.''

Dean said nothing.

"I don't care. Tomorrow hasn't arrived. Winch...."

"Dean. My name's Dean."

Ruby knew if she says Dean's name, she was screwed. But as the song played on the radio, Ruby asked him to dance. 

"Dean. May I have this dance?"

They dance in the side of the road. Underneath the starry skies. 

Ray Charles singing his greatest hit, "Georgia on my Mind."


	3. Chapter 3

They were in their cheap motel room, making love. Usually their trysts were nothing but a roll in the hay, but tonight, they were doing something different. 

Ruby moaned as he thrusted gently into her. He was being soft and tender. Way different from anything he ever did. Not even his old girlfriends did what he was doing. Taking his time. He kissed her as she held him.

Ruby asked him to turn around. She then climbed on top of him. She then pleasured him. They did it for a hour till they were done. 

Afterwards Dean was holding Ruby in his arms, as she was resting on his chest. Ruby couldn't recall Hell, being with Dean, she forgot about it. 

She didn't say it, but those three words weren't spoken. Dean must have known, he holds her closer. 

"Ruby.."

"Matilda. Call me Matilda."

Dean knew that was her human name. The one time he called her that, she punched him. If she allowed that, then she was opening up. At least for tonight.

"Matilda. What do you want to do tomorrow?"

"I don't know. I need a joint. Want to share a blunt?"

They smoked. Dean usually didn't take drugs, he knew Sam did at Stanford, even though he kept denying it. Jessica wasn't totally innocent. Sam told him about the annual Halloween parties they attended. They got pretty wild. Dean teased Sam that if that was their wildest thing, sharing a joint, they needed to get out more. Sam retorted he just needed to keep her safe.

"Sure Sammy. Next time you meet a girl, go crazy and buy a bong."

"Bitch."

"Jerk."

Nothing more was said. Dean and Ruby put out the joint and fall asleep.


	4. Chapter 4

They were on a ferris ride. Neither of them were scared of heights, they seen truly scary things neither one wanted to remember. They were having a blast. The small carnival was cheap and small, but since they were here, why not have fun.

Ruby was annoyed that Dean kept eating her cotton candy. He already ate up her candy apples and popcorn.

"Dean! You said you weren't hungry!"

"I'm not! I'm doing you a favor! You know how many calories are in these things? You said you needed to lose a pound."

"Bullshit. You are just cheap. Fine." She sees a food truck. She got up and "borrowed" his wallet. Dean didn't notice he was too busy checking out some skank wearing skimpy shorts. Ruby made a face. Usually she wouldn't care, but Dean was her date. Bitch winked at him. Ruby gave her a dirty look. The woman seeing Ruby's black eyes, hurried away. Ruby smirked. Bitch better stay away. 

She bought some food. Chili cheese fries and a triple bacon cheeseburger. She also ordered lemonade. Too bad Dean spoiled his appetite. After she returned to the picnic table where Dean was sitting, Dean must have noticed his wallet was missing. Seeing the food, his mouth watered. He just ate, but damn that smelled good. Ruby just smirks at him.

"I'm hungry. Buy your own."

"My wallet. Fine, I'll just share yours."

Ruby didn't protest. She was a demon and didn't need to eat. But she enjoyed the taste of greasy food. Food of today, didn't exist in the thirteenth century. The closest thing was steamed boar and honeycombs to snack on. At least booze existed. 

They went on some more rides, and played many games. Ruby didn't cheat, she could have used her powers, but she didn't want Alistair or Lilith to track her down. She laughed when Dean lost. Dean just gave her a dirty look. He'll show her. He spent another twenty bucks. He won a small dragon. 

"We have a winna!" The obnoxious carnival worker calls. The toy was cheap, probably worth fifty cents, but when he gave into Ruby, he smiled when she squeals in excitement. He blushed when she kissed him on the cheek.

"My hero. He slayed the dragon."

"Yes I did. Matilda, where else. My wallet is getting thin."

"Well, let's replenish it. I seen a pool hall."

When they got there, Ruby said she had a appointment. She promised Dean that it wasn't demon related. Dean understood. He needed to check how things were back home. He called Sam who asked what the hell was he doing. Dean just said he was doing a favor for a friend.

"It's been almost a week. Ruby is missing. I can't sense her, neither can Cas. Hell, I interrogated a demon. Lilith is getting impatient. Lucifer will raise soon."

Dean said nothing. Dammit. They took longer than either realized. If he could, he'll kill Lilith himself grab Ruby and hide in Europe somewhere. Sam would be alright. He can go back to Stanford. Become a lawyer meet some girl, get married and live his life demon free. Bobby and his other hunters can hunt. Dean would retire. Spend the rest of his life with Ruby/Matilda. Shit. He wanted to hit the wall. His eyes stinging, he held his breath trying to catch his breath. The thought of losing her....

"Dean? You still there?"

"Yeah." He tried to hide the shaking in his voice. He knew she was going to die. Either Sam or Dean would have to do it. It was fate. He didn't care anymore she was a demon. She was human once. She made a deal. To save someone she cared about. He told Sam that he had to go. Ruby came in. She was holding a gift.

Ruby was holding a wrapped box. Seeing Dean's face, she asked what's wrong.

"Nothing. Heavy smoke." Ruby didn't believe him, but said nothing. 

"Here. My gift to you."

"It's not going to blow up is it?"

"Of course not. This cost me a lot of time and money. I hope you enjoy it."

Dean opens it. It was a coloured drawing of a woman. She had a tan, fiery red curly hair, a round face and was wearing old fashioned ripped clothing. It was in a silver frame. It read, "To Winchester, Love Matilda."

Dean was touched. 

"Is that you?"

"When I was human. It's not exactly accurate. My eyes were lavender, not green. Many people were scared of me. They thought I was a witch based on my looks. I wanted to pay you back for the dragon."

Dean hugged her. Ruby thought he whispered, I love you too. Ruby holds him, showing him how she felt. The spell broke when demons showed up. Shit! 

"Dean. We have to kill them! If Lilith finds out!"

The fight was tough. No way is either letting them go. No one must know about them. Especially Sam. He was falling for Ruby. She didn't love him, not like Dean. Dean knew about his demon blood addiction, but he didn't care anymore. He killed a demon before he smoked out. After the vessels were dead, he told Ruby they needed to go. Ruby grabbed Dean's present. He forgotten it.

A few years later

Dean was drinking a strong whiskey. After what Cas told him about Ruby, he needed a drink. He was listening to Ray Charles. Everytime this song played, he always changed the radio station or left the area. He told no one about Ruby. No, Matilda. He was staring at her portrait. He was jealous of Jonathan. If Ruby comes back, he was sending her upstairs. After he cured her. She at least deserved it. Michael was in charge. He owed Dean one. He saluted her picture. He fixed it, he paid a professional to make her eyes lavender. 

Sam was watching Dean drink. He was wondering who that woman was. "Georgia on my Mind " was playing. It made Dean angry for some reason. He forbade everyone from playing that song. Sam thought about Ruby. They had a sexual relationship, but no matter how much he tried, she never opened her heart. Sam wondered if she was capable of love. 

Castiel was in the bunker. He wanted to tell Dean a message. "Italy will still be there." Ruby made it clear it was for Dean. To never tell Sam. He didn't judge. Him and Meg had something special. He called him her unicorn.


End file.
